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WO1993025302A1 - Emulsifiant, composition emulsifiante et composition sous forme de poudre - Google Patents

Emulsifiant, composition emulsifiante et composition sous forme de poudre Download PDF

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Publication number
WO1993025302A1
WO1993025302A1 PCT/JP1993/000793 JP9300793W WO9325302A1 WO 1993025302 A1 WO1993025302 A1 WO 1993025302A1 JP 9300793 W JP9300793 W JP 9300793W WO 9325302 A1 WO9325302 A1 WO 9325302A1
Authority
WO
WIPO (PCT)
Prior art keywords
water
parts
soluble
hemicellulose
emulsified
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1993/000793
Other languages
English (en)
Japanese (ja)
Inventor
Hirokazu Maeda
Hitoshi Furuta
Taro Takahashi
Chiemi Takei
Hiroko Kurita
Yoko Sato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fuji Oil Co Ltd (fka Fuji Oil Holdings Inc)
Original Assignee
Fuji Oil Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fuji Oil Co Ltd filed Critical Fuji Oil Co Ltd
Priority to DE69316326T priority Critical patent/DE69316326T2/de
Priority to JP50091494A priority patent/JP3313114B2/ja
Priority to EP93913517A priority patent/EP0598920B1/fr
Priority to US08/193,105 priority patent/US5700397A/en
Priority to AU43558/93A priority patent/AU654443B2/en
Publication of WO1993025302A1 publication Critical patent/WO1993025302A1/fr
Priority to KR94700455A priority patent/KR970005921B1/ko
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/08—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing caseinates but no other milk proteins nor milk fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING OR TREATMENT THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/10—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A23L27/72—Encapsulation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A23L29/262—Cellulose; Derivatives thereof, e.g. ethers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/10—Complex coacervation, i.e. interaction of oppositely charged particles
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/56—Glucosides; Mucilage; Saponins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/80—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in fisheries management
    • Y02A40/81—Aquaculture, e.g. of fish
    • Y02A40/818—Alternative feeds for fish, e.g. in aquacultures
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2989—Microcapsule with solid core [includes liposome]

Definitions

  • the present invention relates to an emulsifier having very good emulsifying properties and emulsion stability, an emulsified composition containing the same, and a powdered composition obtained by pulverizing such an emulsified composition.
  • emulsifiers can be broadly classified into monomolecular emulsifiers and polymer emulsifiers.
  • the former monomolecular emulsifier is a so-called surfactant, and includes fatty acid proof stones, glycerin esters, sugar esters, and the like.
  • These emulsifiers are used by being appropriately blended depending on the use, and various emulsified compositions such as emulsified fragrances, dressings, creams such as coffee cream are produced.
  • a monomolecular emulsifier generally has a problem that it is weak to a change in pH or loses emulsifiability due to a change in concentration due to addition or dilution of a salt.
  • the latter polymer emulsifiers include natural products such as gum-casein represented by arabic gum and synthetic products such as acrylate and polyvinyl alcohol. These polymer emulsifiers are used in the production of emulsified compositions such as emulsified flavors or powdered compositions such as powdered fats and oils and powdered flavors.
  • the powdered composition is produced by emulsifying an oil or a lipophilic fragrance or the like and an aqueous component with a polymer emulsifier, followed by spray drying or the like.
  • the powdered composition may be in the form of microcapsules.
  • arabia gum As the polymer emulsifier, arabia gum, dextrin or modified starch is used.
  • arabic gum is widely used in the field of powdered compositions such as powdered fats and oils and powdered fragrances because of its excellent emulsifying and coating properties.
  • Arabic gum is a purified tree sap
  • dextrin is a low-molecular-weight starch
  • modified starch is a starch derivative obtained by chemically modifying starch.
  • the complex coacervation method is most widely used in industry, and pressure-sensitive copying paper such as non-carbon paper, agricultural chemicals, It is used for micro-encapsulation of pharmaceuticals.
  • the complex coacervation method two dilute aqueous solutions of polycation colloid and polyanion colloid are mixed, and a phase separation is caused between a rich colloid phase and a dilute colloid phase by an electric interaction.
  • This technology uses the rich colloid phase as the encapsulation film.
  • Polycation colloids used in the complex coacervation method include, for example, proteins such as gelatin, gelatin derivatives, albumin, force zein, hemoglobin, and soluble collagen.
  • oncoloids include arabic gum, sodium alginate, carrageenan, tragacanth, potassium propyloxyl methylcellulose, agar, polyvinyl benzene sulfonic acid, polyvinyl methyl ether-maleic anhydride copolymer, Surfactants and the like can be mentioned.
  • Natural polymer emulsifiers are desired. Synthetic products such as polyacrylate / polyvinyl alcohol are often used only for limited reasons, such as problems in emulsifying properties. Although dextrin and modified starch can be supplied stably, when they are used, the film stability of the included substances is inferior to that of gum arabic. In addition, dextrin has a weak emulsifying power and requires the use of other suitable emulsifiers in the production of powdered fats and oils and flavorings.
  • emulsifiers used in various applications must have stable emulsification over a long period of time even when used in final products, and must satisfy the texture when used in foods.
  • gum arabic is widely used as an emulsifier for emulsified fragrances, but as described above, a high concentration is required to obtain a stable emulsified state, and the amount of supply depends on the weather in the producing country. It has the disadvantage that the price fluctuates greatly and the quality is not stable.
  • Xanthan gum or the like is widely used as an emulsifier in dressings, but it has a very high viscosity and does not always have a satisfactory texture.
  • creams such as coffee cream use casein
  • they are not always satisfactory at present, as they are vulnerable to pH changes and destroy emulsions when diluted.
  • polymer emulsifiers used in powdered fats and oils and powdered flavors can be supplied stably and have excellent emulsifying properties during production, as well as the stability of inclusions and the strength of the coating film. However, at present, not all of them are satisfied.
  • the combination of the polycation colloid and the polyanion colloid used in the complex coacervation method may be any combination of the above-mentioned compounds, but it is preferable to select and combine gelatin from the former and arabia gum from the latter. Most suitable and widely used Have been. However, due to recent extreme weather, the production of arabic gum is decreasing. Therefore, the emergence of a polyanion colloid that can be supplied stably instead of arabia gum has been desired. Disclosure of the invention
  • the present inventors have conducted intensive studies in view of the above points and found that if water-soluble hemicellulose obtained by extracting from soybean cotyledons is used as an emulsifier, emulsification, storage stability, PH resistance, salt resistance and temperature resistance A highly complex emulsified composition can be obtained, especially when used in combination with a polycation colloid such as gelatin, and a good composite coacervation can be obtained. Further, when such an emulsified composition is spray-dried, the film strength can be improved. It has been found that a stable powdered and finely powdered composition can be obtained, and that particularly excellent microcapsules can be obtained by drying the composite coacervation. The present invention has been completed based on such findings.
  • an emulsifier containing water-soluble hemicellulose derived from soybean cotyledons as an active ingredient an emulsified composition containing the emulsifier, and a powdered composition obtained by pulverizing the emulsified composition.
  • the water-soluble hemicellulose obtained by extracting from soybean cotyledons preferably has an average molecular weight of several thousand to several million, particularly preferably 5,000 to 100,000.If the molecular weight is too large, the viscosity becomes too high. As the height increases, emulsification becomes difficult. Average molecular weight of hemicellulose this water-soluble is the value determined by the limiting viscosity method you measure the viscosity of NaN0 3 solution of 0. 1 M standard pullulan (Showa Denko KK) as a standard substance . Peronic acid was measured by the Blumenkrantz method, and neutral sugars were measured by the GLC method after alditol acetate conversion.
  • the water-soluble hemicellulose useful in the present invention is extracted from soybean cotyledons, and as a raw material, tofu, soymilk, and okara which is a by-product of producing isolated soybean protein from soybean can be used.
  • a preferred method for producing this water-soluble hemicellulose is as follows. That is, the above-mentioned raw material is heated in an acidic range, preferably in a pH range near the isoelectric point of each protein, preferably at a temperature of 130 ° C or lower and 80 or higher, more preferably 130 ° C or lower 100. The above is thermally decomposed. If the thermal decomposition temperature exceeds 130, the coloration becomes intense due to an increase in low molecular sugars represented by monosaccharides, and the emulsifiability is undesirably reduced. On the other hand, when the temperature is lower than 80 ° C, the amount of extraction is extremely small, which is not preferable.
  • the water-soluble fraction is fractionated and then dried as it is, or, for example, treated with activated carbon, resin adsorption or ethanol precipitation to remove hydrophobic substances or low molecular substances, and dried.
  • a water-soluble hemicellulose can be obtained.
  • the viscosity of the water-soluble hemicellulose solution is, for example, preferably not more than 200 cV, more preferably not more than 100 cV, and still more preferably not more than 50 cV in the case of a 10% aqueous solution. If the degree of misalignment of the water-soluble hemicellulose solution is too high, good emulsification may not be obtained. Therefore, if the molecular weight of the water-soluble hemicellulose is large and the viscosity is too high, it is often effective to reduce the molecular weight before decolorization, deodorization, and drying.
  • the molecular weight reduction treatment can be performed by increasing the heating conditions during the thermal decomposition.However, it should be performed by treating the extraction extract of hemicellulose with alkali, acid, heat, enzymes, etc. Can also.
  • water-soluble hemicellulose is used as an emulsifier for emulsified fragrance, it will be more emulsifying, storage stable, pH resistant, salt resistant, temperature resistant, alcohol resistant, etc. than using arabia gum or modified starch. Stability In addition, an emulsified composition having excellent suspension stability can be obtained. If this water-soluble hemicellulose is used for dressings, it is possible to obtain much less refreshing dressings than when using xanthan gum starch. In addition, by using this water-soluble hemicellulose in creams such as coffee whitener, it is possible to obtain creams that are less likely to undergo emulsification destruction even when the pH is changed or diluted. Can be.
  • This water-soluble hemicellulose can be widely applied to uses other than foods, for example, it can be used for cosmetics such as hand creams and creams for cosmetics and pharmaceuticals. Further, it can also be used as an emulsifying composition for the whole life industry such as an agricultural chemical such as an oil-in-water emulsion-type insecticide or a herbicide, or a printing aid. In this case, the obtained product shows a stable emulsified state for a long period of time, and is stable even after being sprayed, and has excellent durability.
  • water-soluble hemicellulose can be used alone as an emulsifier, but its effect may be further improved by using it in combination with an existing emulsifier, thereby compensating for the disadvantages of various existing emulsifiers. be able to.
  • Existing monomolecular emulsifiers that can be used in combination include various anionic surfactants such as fatty acid stones and nonionic interfaces such as quaternary ammonium salts and other ionic surfactants, glycerin fatty acid esters, and sugar esters.
  • Surfactants and amphoteric surfactants such as lecithin.
  • existing polymer emulsifiers that can be used in combination include natural emulsifiers, such as fuori nori, agar, carrageenan, phaceleran, evening malt seed polysaccharide, tara gum, karaya gum, and pectin.
  • natural emulsifiers such as fuori nori, agar, carrageenan, phaceleran, evening malt seed polysaccharide, tara gum, karaya gum, and pectin.
  • Xanthan gum sodium alginate, tragacanth gum, guagum gum, locust bean gum, pullulan, jielang gum, arabic gum, gelatin, whey and other albumins, casein sodium, various starches And the like.
  • Examples of semi-synthetic pastes include carboxymethyl cellulose (CMC), methylcellulose (MC), hydroxyxetyl cellulose (HEC), propylene glycol alginate, and modified starch represented by soluble starch.
  • examples of the synthetic paste include polyvinyl alcohol and sodium polyacrylate.
  • Sugars such as sucrose and starch syrup, and polyhydric alcohols such as glycerin, D-sorbitol and propylene glycol, and acidulants such as lactic acid, vinegar, citric acid, and malic acid are added to the aqueous phase. Doing so may improve stability.
  • Additives such as an anti-fading agent such as L-ascorbic acid or a derivative thereof, and an amino-caprolponyl reaction product, and an antiseptic can also be used.
  • the oil phase used in the emulsified composition of the present invention is not particularly limited as long as it is an oily substance that is hardly soluble in water, and examples thereof include general oils and fats, oil-soluble flavors, oil-soluble pigments, waxes, insecticides, and the like. Herbicides, oil-soluble drugs, oil-soluble reagents, and the like. If a long-term suspension stability is required even when the emulsion is diluted and used, as in the case of emulsified flavors, use a specific gravity regulator with a specific gravity of 1 or more to increase the specific gravity. Is preferred.
  • the specific gravity adjuster examples include brominated oil, sugar esters represented by sucrose acetate isobutyrate (SA IB), dammar resins, rosin, ester gum and the like. Therefore, the present invention relates to foods such as emulsified fragrances, dressings or creams , cosmetic mouths such as hand creams , pharmaceuticals such as paints, pesticides such as insecticides, or printing. It can be widely used in general living industries represented by auxiliaries.
  • the emulsifier according to the present invention also has a function as a powdered base material, and includes a case where the emulsifier is used as a powdered base material.
  • water-soluble hemicellulose can be used alone as a polyanion colloid, but when used in combination with an existing polyanion colloid, the disadvantages of the existing polyanion colloid can be obtained.
  • existing polyanion colloids include lab gum, sodium alginate, carrageenan, tragacanth gum, carboxymethylcellulose, agar, polyvinylbenzene sulfonic acid, and polyvinyl methyl ether-anhydrous, as described above.
  • Maleic acid copolymers, surfactants and the like can be mentioned.
  • the weight ratio of the combination of gelatin and water-soluble hemicellulose is from 10: 1 to 1:10, preferably in the range from 2: 1 to 1: 2.
  • concentrations of gelatin and water-soluble hemicellulose must be below a certain concentration, and the concentration of a mixture of both colloids is below 10%, preferably below 4%. It is desirable that However, it is also possible to generate a coacervate by dispersing or emulsifying the core material of the microforce in a high-concentration colloid solution before diluting it to a predetermined concentration.
  • the aforementioned gelatin and water-soluble hemicellulose mixture coid ,, liquid are coacervated by gradually acidifying the liquid to a pH below the isoelectric point of gelatin while maintaining the temperature above the gel point of gelatin. Is formed and the solution When the temperature is lowered below the gel point of gelatin, microcapsules surrounding the core substance are formed.
  • any of inorganic acids and organic acids can be used as long as they are water-soluble. However, regardless of which acid is used, if this is gradually added dropwise as a dilute solution, the formation of a coacervate is favorably performed.
  • the microcapsules thus obtained are water-soluble colloids and can be used as they are in aqueous systems.
  • a curing agent examples include aldehydes such as formaldehyde, glutaraldehyde, mucochloric acid, glyoxal, glycerin aldehyde, and acrolein, 0-benzoquinone, p-benzoquinone, and cyclohexane.
  • Examples include diketones such as xan-1,2-dione, tannic acid, gallic acid, and ferric salt.
  • formaldehyde and glutaraldehyde are particularly preferably used.
  • the time required for curing can be appropriately selected depending on the desired elution rate of the core substance.
  • the prepared microcapsules can be double coated with another coating agent to adjust the dissolution rate of the core substance, reinforce the microcapsule wall, and prevent pinholes. Double coating is achieved by dissolving the coating substance in a microforce suspension before or after hardening, changing the liquid properties, or causing the coating substance to become insolubilized by adding other substances. Is done.
  • the coating substance include cellulose derivatives such as benzylaminomethylcellulose and getylaminomethylcellulose, vinyl acetylamine-vinyl acetate copolymer, polyvinyl acetal getylaminoacetate, and polyethylethyl acetate.
  • Cellulose acetate a neutral or alkaline water-insoluble compound that is soluble in water, such as polyvinyl derivatives such as aminomethylstyrene. Dissolves in water with a neutral property, such as cellulose derivatives such as tophthalate and cellulose acetate succinate, and polyvinyl derivatives such as polyvinyl alcohol phthalate and polyvinyl acetate phthalate.
  • cellulose derivatives such as tophthalate and cellulose acetate succinate
  • polyvinyl derivatives such as polyvinyl alcohol phthalate and polyvinyl acetate phthalate.
  • Compounds that form insoluble salts such as acidic and water-insoluble compounds, sodium alginate, potassium propyloxymethylcellulose, and resin base materials such as water-soluble methylol compounds whose condensation is in the initial stage.
  • the core substance used in the microcapsule of the present invention may be any oil-soluble substance or solid particles that are hardly soluble in water, and may be any of general oils and fats, oil-soluble fragrances, oil-soluble pigments, and waxes. And water-soluble drugs, insecticides, herbicides, oil-soluble drugs, oil-soluble reagents, starch powder, silica gel, glass beads and the like. Therefore, the present invention relates to foods such as edible flavors, dressings or creams, artificial feeds such as fish feed, industrial products such as pressure-sensitive copying paper and printing flavors, hand creams and the like. It can be widely used in general industries such as cosmetics, fragrances and other toys, products such as sustained-release medicines, pesticides such as insecticides, and fertilizers.
  • coacervation base in the present invention can be used for beverages as it is.
  • water-soluble hemicellulose (c) was obtained in the same manner as described above without treatment with an activated carbon column.
  • a trial production of an emulsified fragrance was carried out in exactly the same manner as in Example 1 except that water-soluble soybean hemicellulose (mouth) was used instead of water-soluble soybean hemicellulose (a). The properties were good. In addition, the stability of the orange-like soft drink made with this flavor is good. It was good.
  • Example 1 an emulsified fragrance was produced in the same manner as in Example 1 except that water-soluble soybean hemicellulose (c) was used instead of water-soluble soybean hemicellulose (c). The properties were good. Also, the stability of the orange-like soft drink made with this flavor was good.
  • a trial production of an emulsified fragrance was conducted in exactly the same manner as in Example 1 except that arabic gum was used instead of using water-soluble soybean hemicellulose (a). Separation was already observed in one month. .
  • An emulsified perfume was prepared in exactly the same manner as in Example 1 except that in place of using water-soluble soybean hemicellulose (a), a chemically modified starch (Pyulity Gum, Oji National Co., Ltd.) was used. At that time, sedimentation and gelation were already observed in one month.
  • a chemically modified starch Pyulity Gum, Oji National Co., Ltd.
  • An emulsified perfume was prepared in exactly the same manner as in Example 1, except that in place of using water-soluble soybean hemicellulose (a), arabinogalactan (manufactured by Mitsubishi Rayon Co., Ltd.) derived from western larch was used. When I tried to do so, it immediately separated into two layers and could not be emulsified.
  • a water-soluble soybean hemicellulose
  • arabinogalactan manufactured by Mitsubishi Rayon Co., Ltd.
  • dietary fiber (“Selfer", manufactured by Japan Food Processing Co., Ltd.) is a woven fabric obtained by removing starch, proteins, lipids, etc. from the corn hulls. After autoclaving (140 ° C, 60 minutes), heat extraction, centrifugation (500G, 10 minutes) to obtain supernatant, and ethanol concentration becomes 60% As in ethanol I got it. The precipitate was recovered by centrifugation (500 G, 10 minutes), and dried to obtain a water-soluble cone hemicellulose.
  • Glucose 7.4 An emulsified perfume was prepared in exactly the same manner as in Example 1 except that water-soluble soybean hemicellulose (a) was used in Example 1 instead of using water-soluble corn hemicellulose as described above. The emulsion particle size was large and no suspension stability was obtained.
  • the average particle size is measured by a laser diffraction particle size distribution analyzer (LA-500:
  • Emulsion dressing was performed in exactly the same manner as in Example 4 except that 0.4% of xanthan gum was used in place of water-soluble soybean hemicellulose (a) in Example 5 and the reduced amount was supplemented with water. A prototype was produced, but the viscosity was very high.
  • Example 7 4 parts of water-soluble soybean hemicellulose (a) and 2 parts of commercially available casein sodium were dissolved in 75 parts of water.
  • 20 parts of purified coconut oil containing 0.1 part of a commercially available milk flavor (Milk FT-0113, manufactured by Takasago International Corporation) was added at 70 ° C, and pre-emulsification was performed with a homomixer.
  • the mixture was emulsified (500 kgf / cm 2 ) with a high-pressure homogenizer to obtain a white toner for coffee.
  • This white toner had an average particle size of 0.5 fim, maintained a stable emulsified state, and was stable even after storage for one month.
  • coffee containing 8% sugar prepared to pH 6.8 with sodium bicarbonate
  • a sugar solution prepared by dissolving 15 parts of granulated sugar in 15 parts of water and an oil phase obtained by dissolving 1 part of polyglycerin-condensed ricinoleate in 20 parts of orange oil are emulsified using a homogenizer to form a WZO emulsion.
  • a solution prepared by dissolving 50 parts of water-soluble soybean hemicellulose (mouth) in 450 parts of water and adjusting the pH to 4.0 with citric acid and the whole amount of the WZO-type emulsion obtained earlier were pre-emulsified with a homomixer, The mixture was emulsified and mixed using a homogenizer to obtain a W / 0 / W emulsion.
  • Example 1 2 Dissolve 10 parts of water-soluble soybean hemicellulose (a) in 80 parts of water, disperse 10 parts of orange oil (Yankei Sangyo Co., Ltd.) to 100 parts, and emulsify with a homogenizer (200 kgf / cm) 2 ) I did. This emulsion maintained a stable emulsified state despite no addition of an emulsifier. Thereafter, this emulsion was spray-dried to prepare a powdered flavor. Observation of the dried powder with a scanning electron microscope revealed that the powder was in a good microcapsule state.
  • a powdered flavor was produced in the same manner as in Example 12 except that water-soluble soybean hemicellulose (mouth) was used instead of water-soluble soybean hemicellulose (a).
  • the emulsifying properties and film properties were extremely good.
  • Example 12 a powdered flavor was produced in exactly the same manner as in Example 12 except that water-soluble soybean hemicellulose (c) was used instead of water-soluble soybean hemicellulose (c). The emulsifiability and film properties were very good. ⁇
  • a powdered flavor was prepared in the same manner as in Example 12 except that gum arabic was used in place of water-soluble soybean hemicellulose (a). Although it was good, it was inferior to water-soluble soybean hemicellulose (a). Comparative Example 7
  • a powdered fragrance was produced in the same manner as in Example 12 except that dextrin (Pinedex, Matsutani Chemical Co., Ltd.) was used instead of water-soluble soybean hemicellulose (a).
  • dextrin Pinedex, Matsutani Chemical Co., Ltd.
  • water-soluble soybean hemicellulose a
  • a powdered flavor was prepared in the same manner as in Example 12 except that a modified starch (Cabsur, Oji National Co., Ltd.) was used instead of water-soluble soybean hemicellulose (a).
  • the prepared emulsion had good emulsifiability, but was inferior in film properties and aroma, and inferior in antioxidant properties.
  • Oxidation is defined as limonene epoxide (mg / g LIMONENE), which is an indicator of terpene substance oxidation.
  • Example 15 powdered fats and oils were produced in exactly the same manner as in Example 15 except that water-soluble soybean hemicellulose (mouth) was used instead of water-soluble soybean hemicellulose (a). The emulsifiability and film properties were extremely good.
  • Example 15 powdery fats and oils were produced in exactly the same manner as in Example 15 except that water-soluble soybean hemicellulose (c) was used instead of water-soluble soybean hemicellulose (c). The chemical properties and film properties were extremely good. ⁇
  • Example 15 a powdery fat was made in exactly the same manner as in Example 15 except that arabic gum was used instead of using water-soluble soybean hemicellulose (a). Although the properties were good, it was inferior to water-soluble soybean hemicellulose (a). Comparative Example 10
  • Powdered fats and oils were prepared in the same manner as in Example 15 except that dextrin (Pinedex, Matsutani Chemical Co., Ltd.) was used in place of water-soluble soybean hemicellulose (a). Although it was produced, good microcapsules could not be prepared because of its poor emulsifying property. Comparative Example 1 1
  • the powdered fats and oils were prepared in the same manner as in Example 15 except that a modified starch (Cabsur, Oji National Co., Ltd.) was used instead of water-soluble soybean hemicellulose (a). Although the emulsifying property was good when it was manufactured, it was inferior in terms of film properties and aroma, and inferior in terms of gas-barrier properties.
  • microcapsules After the coacervate is formed, cool to 5 ° C to prepare microcapsules. After preparing the microcapsules, the supernatant was filtered, washed with cold water, suspended in cold water and spray-dried to obtain a microencapsulated flavor of orange oil. Next, 120 parts of granulated sugar was dissolved in 880 parts of water, and the pH was adjusted to 3.0 using a 50% citric acid solution. Subsequently, 0.2 parts of the microencapsulated flavor was added to obtain an orange-like soft drink. The beverage was quite stable after 3 months. The microencapsulated fragrance was stable even when stored refrigerated for three months.
  • Prototype of microencapsulated flavor was produced in exactly the same manner as in Example 18 except that water-soluble soybean hemicellulose (mouth) was used instead of water-soluble soybean hemicellulose (a). The stability was good. In addition, the orange-like soft drink made with this flavor had good stability.
  • Prototype of microencapsulated fragrance was prepared in exactly the same manner as in Example 18 except that water-soluble soybean hemicellulose (c) was used instead of water-soluble soybean hemicellulose (c). The stability was good. In addition, the orange-like soft drink made with this flavor had good stability. The microencapsulated fragrance is not The results were not inferior to those performed using arabia gum instead of using water-soluble soybean hemicellulose (a).
  • Example 18 The procedure of Example 18 was repeated, except that in place of using water-soluble soybean hemicellulose (a), 1 part of sodium alginate was dissolved in 89 parts of water and used.
  • a water-soluble soybean hemicellulose
  • the forcepsellated fragrance was prepared, it was recognized that the fragrance was immediately separated from the orange-like soft drink made with this fragrance, and that the preparation of microcapsules was insufficient.
  • the state after storage of the cellulosic flavor and orange-like soft drink at 5 ° C for 90 days was observed. The results are shown in comparison.
  • the average particle size is measured using a laser diffraction particle size distribution analyzer (LA-500).
  • the microcapsules were added dropwise to a 0.1% calcium chloride solution while stirring and suspending, and double coated. After the double coating, the microcapsule feed was prepared by washing with water, filtering and dehydrating, and drying with air at 50 ° C. The resulting microcapsule feed was fed to 10 goldfish, and the survival rate was observed. For the purpose of comparison, a commercial feed (Angel Color Fried; Nippon Pet Food Co., Ltd.) was given to 10 goldfish in the same amount as in Example 21.
  • Example 2 1 vs. Akira Survival number Survival rate (%) Survival number Survival rate) Feeding 1 say 10 100 10 100 feeding ⁇ day 10 100 10 100 feeding 30 saying 10 100 10 100 90 days after feeding 9 90 10 100 or more Thus, when using water-soluble soybean hemicellulose, a good microcapsule feed could be prepared.
  • the prepared microcapsules were applied at a dry weight of 5 g / m 2 .
  • Other papers have a coloration of 100 parts of 5-phenylsalicylic acid zinc salt and 30 parts of styrene / butylene latex (50% solids) dispersed in 200 parts of water. The composition was applied to a concentration of 5 g / m 2 . When these two papers were overlapped so that the pressure-sensitive printing portions faced each other and pressed with a pencil, a clear color development was observed in the pressed portion.
  • Example 23 When the microencapsulated fragrance obtained in Example 23 was applied to paper and rubbed with a finger, an orange flavor was successfully released. The flavor retained well after 90 days and was released by rubbing with a finger.
  • the coacervate When the coacervate was formed, it was cooled to 5 ° C, 1 ml of a 37% formaldehyde solution was added, and the mixture was stirred for 1 hour. Then, the pH was adjusted to 9 by adding 2N-sodium hydroxide. Next, the liquid temperature was raised to 50 ° C and a curing treatment was performed for 12 hours. After the curing treatment, a solution prepared by dissolving 30 parts of cellulose acetate phthalate in 700 parts of alkaline water at pH 9 was added, the pH was adjusted to 5.0 with 10% hydrochloric acid with stirring, and the mixture was stirred at 20 ° C for 1 hour. .
  • microencapsulated herbicide thus obtained was washed with water, filtered, and then dried at 50 ° C with ventilation. This microencapsulation Degradation of the herbicide active ingredient hardly occurred, and the herbicidal effect was examined after application to the soil, and satisfactory results were obtained.
  • the emulsified flavor is stable over a long period of time even in the beverage of the final product. It does not become expensive and can give a very smooth emulsified dressing. In addition, it has become possible to create creams that are resistant to pH changes. On the other hand, it was found that it can be effectively used for emulsifying cosmetics, pharmaceuticals, agricultural chemicals, industrial oils, and the like. In addition, when water-soluble hemicellulose derived from soybean cotyledons was used as a powdered base for lipophilic substances, effects excellent in emulsifying properties, film properties and antioxidant properties were obtained.

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Abstract

Emulsifiant renfermant une hémicellulose soluble à l'eau, dérivée du cotylédon de soja, composition émulsifiante remarquablement stable renfermant l'émulsifiant susvisé et composition sous forme de poudre, que l'on élabore en réduisant la composition susvisée en poudre.
PCT/JP1993/000793 1992-06-16 1993-06-14 Emulsifiant, composition emulsifiante et composition sous forme de poudre Ceased WO1993025302A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DE69316326T DE69316326T2 (de) 1992-06-16 1993-06-14 Emulgiermittel, emulgierende Zusammensetzung und pulverige Zusammensetsung
JP50091494A JP3313114B2 (ja) 1992-06-16 1993-06-14 乳化剤及び乳化組成物並びに粉末化組成物
EP93913517A EP0598920B1 (fr) 1992-06-16 1993-06-14 Emulsifiant, composition emulsifiante et composition sous forme de poudre
US08/193,105 US5700397A (en) 1992-06-16 1993-06-14 Emulsifier, emulsion composition, and powder composition
AU43558/93A AU654443B2 (en) 1992-06-16 1993-06-14 Emulsifier, emulsifying composition and powdery composition
KR94700455A KR970005921B1 (en) 1992-06-16 1994-02-15 Emulsifier, emulsion composition and powdery composition

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JP22187992 1992-06-16
JP22188092 1992-06-16
JP4/221879 1992-06-16
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JP33526792 1992-11-20
JP4/335267 1992-11-20

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CA (1) CA2115145C (fr)
DE (1) DE69316326T2 (fr)
WO (1) WO1993025302A1 (fr)

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AU4355893A (en) 1994-01-04
DE69316326D1 (de) 1998-02-19
EP0598920A1 (fr) 1994-06-01
AU654443B2 (en) 1994-11-03
EP0598920A4 (fr) 1994-12-21
EP0598920B1 (fr) 1998-01-14
KR970005921B1 (en) 1997-04-22
US5700397A (en) 1997-12-23
JP3313114B2 (ja) 2002-08-12
DE69316326T2 (de) 1998-08-13
CA2115145C (fr) 1999-04-20
CA2115145A1 (fr) 1993-12-23

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